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542 Holiday homes in Siena Province

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542 Results  |  
13 Photos

Cottage | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £212 /night

£1484 - £2067 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
  • Private garden
Podere Le Lame is an enchanting Tuscan Mill house, set in four hectares of olives - a house for complete peace and relaxation. All bedrooms have en suite bathrooms with power showers. There is a large hall/dining/kitchen with an open fire and French windows to a loggia.  …see more

24 Photos

Cottage | 2 Bedrooms | sleeps 5

Excellent 5/5 

5 Nights min stay

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from £44 /night

£307 - £368 / week

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Key info:

  • Nearest beach 75 km
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
HOME / COTTAGE INDEPENDENT OF NEW CONSTRUCTION IN THE OPEN COUNTRYSIDE panoramic view on San Gimignano Pets: maximum 2 (small)  …see more

22 Photos

Apartment | 1 Bedroom | sleeps 2

Good 3/5 

1 night min stay

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from £53 /night

£368 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Ideal romantic nest house in the middle of luscious green Tuscan countryside with superb views and possibility of outdoor life. Suìtable in all seasons aqs the basis for visiting Siena Florence and all the nearby historical Tuscan sites.  …see more

Featured properties

16 Photos

Farmhouse | 1 Bedroom | sleeps 4

Short stays welcome

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from £64 /night

£446 - £536 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Romantic one bedroom apartment in a converted traditional Tuscan farmhouse between San Gimignano and Volterra. Beautifully renovated farm building, Terraces with fantastic views, pool, ideal for rest and relaxation! Easy access Siena , Pisa and Florence.  …see more

21 Photos

Apartment | 2 Bedrooms | sleeps 6

1 night min stay

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from £91 /night

£631 - £1472 / week

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Key info:

  • Nearest beach 84 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Charming holiday apartment in heart of Tuscany; excellent for families and couples seeking relaxation. Just few minutes to Siena, San Gimignano and Florence. Pool and fresco dining area.  …see more

22 Photos

Villa | 3 Bedrooms | sleeps 5

Excellent 5/5 

3 Nights min stay

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from £154 /night

£1074 - £1621 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
  • Private garden
3 BDR cosy house with patio,small pool,AC,Wifi, in the heart of Siena countryside, nestled in a village Please,ALWAYS enquiry about prices.  …see more

19 Photos

Guest house | 3 Bedrooms | sleeps 5

Excellent 5/5 

3 Nights min stay

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from £63 /night

£439 - £701 / week

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Key info:

  • Nearest beach 60 km
  • Suitable for over 5s only
  • Car advised
  • May take pets – please enquire
Spacious thirteenth century town house built right on the walls of the historic centre of Radicondoli, perfect for family or couple. Stunning views at all three levels of this historic building.  …see more

18 Photos

Villa | 3 Bedrooms | sleeps 6

Short stays welcome

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from £137 /night

£955 - £1831 / week

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Key info:

  • Nearest beach 50 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
The Piaggione of Serravalle is like a gateway entrance that protects an uncontaminated hill that seems lost in time and where nature apparently undisturbed articulates its own natural rhythms. Located on one of the highest summits of Chianti, in between Siena and Floren  …see more

20 Photos

Farmhouse | 4 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

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from £103 /night

£716 - £1060 / week

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Key info:

  • Nearest beach 100 km
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
Spectacular Views! Well equipped apartment in great location.Great for families. Outside, is a very attractive pergola, with BBQ for drinks and meals, overlooking the beautiful Tuscan hills and valleys. Vouchers for the local spa are provided upon request. Logs for the fire are provided free of charge.  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 8

3 Nights min stay

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from £90 /night

£626 - £687 / week

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Key info:

  • Nearest beach 90 km
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Large, elegant, comfortable apartment in incomparable surroundings. Peaceful and relaxing with spectacular scenery. 3 km from Castellina in Chianti with its medieval town centre, shops, bars, restaurants. 22 km from Siena., 37km from Florence. No neighbours or noise. Perfect to come home to after the day's excursions. A glass of wine in the garden, dinner under the stars.  …see more

24 Photos

Villa | 8 Bedrooms | sleeps 16

Excellent 5/5 

3 Nights min stay

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from £447 /night

£3128 - £5007 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
  • Private garden
8 BDR luxury historical villa with garden and pool in the heart of Siena countryside nestled in a village. Please,ALWAYS,enquiry about prices.The house can be rented just in part (4BDR).  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

4 Nights min stay

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from £221 /night

£1541 - £3960 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
  • Private garden
5 BDR beautiful indipendent house with pool,AC,WiFi in the Siena countryside, close to a village. Please,ALWAYS enquiry about prices.The house can be rented just in part (3BDR apt))  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 7

3 Nights min stay

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from £182 /night

£1271 - £1621 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
The villa is the ideal starting point to visit the Val di Chiana and Val d'Orcia with its wonderful medieval towns such as Cortona, Montepulciano, San Quirico d'Orcia, Pienza, as well as Montalcino and San Gimignano and the beautiful art cities of Siena and Florence.  …see more

16 Photos

Apartment | 2 Bedrooms | sleeps 5

Excellent 5/5 

1 night min stay

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from £79 /night

£552 - £675 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
In the middle of the Siena hills facing the Cecina valley, Ulivo is situated within the villa of Il Bel Canto at a short distance from Volterra, San Gimignano, Siena & the sea coast. Ideal for relacing and enjoying the beautiful 360 degrees view.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 7

Very Good 4/5 

4 Nights min stay

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from £142 /night

£992 - £1984 / week

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Key info:

  • Nearest beach 110 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Self-catering villa with stunning views over Tuscany vineyards. Private pool. Shared tennis court with villa LisiDor (#44909, same owner). Internet. Bbq and shaded eating area. Fenced garden. Midway to Siena and Florence Typical Tuscan countryside with private pool and garden in silent position in the middle of Chianti hills  …see more

24 Photos

Farmhouse | 7 Bedrooms | sleeps 16

Very Good 4.5/5 

1 night min stay

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from £63 /night

£439 - £4030 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Swimming pool 15x5mt, cleaned using salt not chlorine. 3D archery range with wild animal targets, bow rental and trainer available. Try Alessandro's traditional cousine, it will surprise you! Our cellar and vineyards are open for visit, taste our Rosso di Montepulciano  …see more

20 Photos

Apartment | 3 Bedrooms | sleeps 9

Excellent 5/5 

1 night min stay

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from £171 /night

£1196 - £1472 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
Enjoy the view, meanwhile swimming in the pool, dine in the outside garden watching the beautiful sunset vew,in front of the chimney during the winter in the comfort of the heated pavements.  …see more

20 Photos

Apartment | 4 Bedrooms | sleeps 9

1 night min stay

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from £149 /night

£1043 - £1227 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
On the ground floor of a 1600 Villa ,completely renovated for the maximum comfort of guests. All windows facing the valley and the natural reserve below.50 square meter private terrace with incredible view on the countryside.15x4 meter swimming pool .  …see more

24 Photos

Farmhouse | 3 Bedrooms | sleeps 6

1 night min stay

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from £69 /night

£482 - £1577 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Wonderful place to relax, make sports ( walking,archery and swimming) sip our good wine and enjoy our cousine. Our swimming pool is 15x5mt wide and is cleaned using salt and not chlorine.  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 4

Excellent 5/5 

1 night min stay

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from £71 /night

£491 - £614 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
A 2 rooms apartment, with a double/twin bedroom, large bathroom with shower and jacuzzi bathtub, large sitting room with a double sofa bed, dining area with kitchen corner, fully furnished with oven. Chimney, satellite tv, wifi. salty water swimming pool.  …see more

16 Photos

Farmhouse | 6 Bedrooms | sleeps 20

Excellent 5/5 

2 Nights min stay

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from £526 /night

£3680 - £5081 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
Climatized villa with swimming pool, wi-fi,and TV with Sky channels, offers relax and fun at only 7 miles from Siena. The Count Filippo Fiorentini, English speaking will welcome you with a good glass of wine, in his villa.  …see more

22 Photos

Apartment | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £50 /night

£347 - £1096 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
ARCOBALENO 110 m2 - 6 Guest . coveredy by free Wi-Fi Charmed Villa located 1km far from Radda in Chianti, Siena-Tuscany, in the heart of the Chianti Classico- with private garden, indipendent entrance, tv/sat, free WI-FI nternet connection and swimmingpool.  …see more

19 Photos

Farmhouse | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £51 /night

£351 - £614 / week

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Key info:

  • Nearest beach 50 km
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
In the Crete Senesi, a working organic farm focused on breeding/training thoroughbred horses. The two traditional farmhouses are beautifully furnished with family pieces. The Rapolano thermal spas are just a few minutes' drive, and Siena is within easy reach. A traditional farmhouse with a medieval tower and a water mill.  …see more

22 Photos

Villa | 3 Bedrooms | sleeps 8

3 Nights min stay

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from £188 /night

£1315 - £1840 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Traditional Farmhouse / Villa In Siena (Tuscany) with stunning views. A place to create memories.  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 14

5 Nights min stay

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from £470 /night

£3290 - £3965 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
Sleeps 14 with possibility to add adjacent apartments up to total of 33. A beautiful 15th-century villa in the heart of the Chianti countryside, with 360° uninterrupted views of olives, vines and forests, with amazing sunset views over San Gimignano and the Apennines  …see more

11 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

2 Nights min stay

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from £54 /night

£377 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
The house offers everything you need for a relaxing holiday and has free Wi-Fi, microwave oven, drip coffee maker, toaster and kettle as well as being supplied with all bedroom and bathroom linen.  …see more

14 Photos

Apartment | 1 Bedroom | sleeps 3

3 Nights min stay

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from £32 /night

£220 - £439 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • No pets allowed
nice and comfortable apartments in walking distance from the village  …see more

9 Photos

Apartment | 1 Bedroom | sleeps 3

3 Nights min stay

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from £61 /night

£425 - £539 / week

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Key info:

  • Suitable for over 5s only
  • Car advised
  • Air conditioning
  • No pets allowed
Siena Apartments with easy access to the town centre  …see more

19 Photos

Villa | 4 Bedrooms | sleeps 10

7 Nights min stay

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from £188 /night

£1315 - £1884 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
The villa near Pienza is elegantly furnished, in a perfect combination between comfort and tradition, with modern amenities such as internet Wi-Fi and Sat-TV. On two floors, the house can host up to 10 people.  …see more

20 Photos

Villa | 6 Bedrooms | sleeps 10

7 Nights min stay

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from £226 /night

£1577 - £2979 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
This beautiful villa in Siena is situated on the hills with a breathtaking view over the vineyards up to Siena. An ideal accommodation for all those seeking peace and quiet but also a perfect point of departure for visiting the beautiful attractions of the Chianti  …see more

13 Photos

Apartment | 2 Bedrooms | sleeps 5

3 Nights min stay

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from £39 /night

£272 - £517 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Nice and comfortable apartments in walking distance from the village  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 18

7 Nights min stay

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from £261 /night

£1823 - £4643 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Splendid villa with breathtaking view over the Castle of Strozzavolta, in the Chianti, between Florence and Siena.  …see more

19 Photos

Villa | 4 Bedrooms | sleeps 7

Very Good 4/5 

3 Nights min stay

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from £84 /night

£587 - £1017 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
Gorgeous holiday villa in Siena, just 5 minutes walking from the town. blloming garden, shared swimming pool, private car parking, internet (with flash drive), laundry room, chef for dinner or meal on request  …see more

17 Photos

Apartment | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £44 /night

£307 - £614 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
Stunning apartments for holiday rental in Torrita di Siena, near Pienza and Montepulciano  …see more

6 Photos

Villa | 2 Bedrooms | sleeps 6

2 Nights min stay

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from £163 /night

£1139 - £1577 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
Unique villa in the area of Siena, pefect climatized and furnished with all comforts,The villa le Tortore offers private parking , private garden, exclusivity, access to the swimming pool, air conditioning, satellite Tv with Sky channels, PC with free dsl and wi-fi.  …see more

9 Photos

Farmhouse | 4 Bedrooms | sleeps 16

2 Nights min stay

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from £376 /night

£2629 - £3505 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
The Podere Podernovo offers accomodation up to 16 people,with all comforts,as heating, air condititioning, Internet,wi-fi, Tv with Sky.The Count Fiorentini will welcome you in his farmhouse just 12 km south of Siena in the Arbia valley.  …see more

12 Photos

Villa | 3 Bedrooms | sleeps 7

7 Nights min stay

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from £251 /night

£1753 - £2103 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
As the house is part of a company that produces Brunello di Montalcino is possible to follow the stages of production or do a tasting tour to discover one of the best wines in the world in our cave.  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 2

1 night min stay

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from £53 /night

£368 - £859 / week

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Key info:

  • Nearest beach 84 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Self catering holiday apartments in heart of Tuscany; excellent for families and couples seeking relaxation. Just few minutes to Siena, San Gimignano and Florence. Pool and fresco dining area. In our restaurant is possible to take: Breakfast Dinner Wine tasting  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 4

Min stay varies

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from £114 /night

£798 - £1043 / week

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Key info:

  • Nearest beach 84 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Self catering holiday apartments in heart of Tuscany; excellent for families and couples seeking relaxation. Just few minutes to Siena, San Gimignano and Florence. Pool and fresco dining area. In our restaurant is possible to take: Breakfast Dinner Wine tasting  …see more

19 Photos

House | 15 Bedrooms | sleeps 30

Min stay varies

Add to shortlist

Key info:

  • Nearest beach 84 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
Poggiarello is a special place to spend a charming holiday in close contact with nature, where is possible to reach in few minutes Siena, San Gimignano, Firenze, Pisa, Lucca, Monteriggioni,Montalcino.  …see more

20 Photos

Apartment | 3 Bedrooms | sleeps 8

1 night min stay

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from £53 /night

£368 - £1963 / week

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Key info:

  • Nearest beach 84 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Self catering holiday apartments in heart of Tuscany; excellent for families and couples seeking relaxation. Just few minutes to Siena, San Gimignano and Florence. Pool and fresco dining area. In our restaurant is possible to enjoy: Breakfast Dinner Wine tasting  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 11

5 Nights min stay

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from £248 /night

£1735 - £3715 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
Splendid 18th century mansion with typical Sienese architecture. It is situated next to the historical village of Basciano. The house position is ideal because one reaches the Chianti region in a few minutes or can enjoy the culture and convenience of the city of Siena.  …see more

11 Photos

Villa | 3 Bedrooms | sleeps 8

Excellent 5/5 

Min stay varies

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Key info:

  • Nearest beach 62 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
L fienile di Colletalli is an ancient barn restored and converted into the most beautiful and unique spa resort. Is just five minutes by car from middle-age village Radicondoli. A large living room, a private and exclusive beautiful farm, a terrace, a garden, and a pool  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

Very Good 4/5 

1 night min stay

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from £113 /night

£789 - £1139 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Zafferano, ideal for a self catering holiday, is found in the hamlet of Vergelle, set amongst the peaceful countryside known as the Crete Senesi, south of Siena, in Tuscany. It is close to the hilltop town Montalcino with its world famous Brunello vineyards. This large 4 bedroomed villa is part of Vergelle’s old school building, and was fully renovated in 2008.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £1502 /night

£10513 / week

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Key info:

  • Nearest beach 20 km
  • Swimming pool
  • Suitable for over 5s only
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
The first floor of a Villa dating from around 1760, a commanding position within a protected area of outstanding natural beauty. Described as 'Manhattan in Tuscany' the compassionate treatment of the lovely old structure is supercharged by contemporary interior design. Bright, spacious and fully equipped for entertainment and comfort. A/C,Plasm TVs, WiFI, home theatre, stereo  …see more

20 Photos

Farmhouse | 8 Bedrooms | sleeps 25

Very Good 4.5/5 

Min stay varies

Add to shortlist

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
"The Harvest Moon" holiday house, is a Tuscan country mansion with a spectacular pool overlooking the boundless valley. The whole property is available for more comfort and privacy. The whole property is available for more confort and privacy.  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 6

Short stays welcome

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from £149 /night

£1043 - £1831 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
The Piaggione of Serravalle is like a gateway entrance that protects an uncontaminated hill that seems lost in time and where nature apparently undisturbed articulates its own natural rhythms. Located on one of the highest summits of Chianti, in between Siena and Floren  …see more

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Farmhouse | 8 Bedrooms | sleeps 19

2 Nights min stay

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from £285 /night

£1989 - £2988 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
A 17th century stone hamlet situated in one of the most wonderful positions of Tuscany. Four apartments and two bedrooms furnished with big taste and with exclusive period furniture, fireplace Sky TV independent heating external private space. Parking, scenic pool  …see more

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Farmhouse | 4 Bedrooms | sleeps 8

2 Nights min stay

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from £118 /night

£820 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
On the sweet hills of the Chianti shire between vineyardand and olive groves, stands the "Podere il Pino". It offers a spectacular view on the beautiful medieval village of San Gimignano and it is very close to art cities as Florence, Siena, Pisa, Volterra and the sea.  …see more

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Farmhouse | 1 Bedroom | sleeps 4

Short stays welcome

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from £58 /night

£400 - £650 / week

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Key info:

  • Nearest beach 45 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Self catering Farmhouse with 4 luxury apartments in rural Tuscany with swimming pool spectacular views ,nearby golf, walking, trekking, fishing, biking. San Gimignano, and Certaldo, 20 minutes drive, Florence, Siena and Pisa one hour from the house.  …see more